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Sequential Copper-Catalyzed Vinylation/Cyclization: An Efficient Synthesis of Functionalized Oxazoles

Rubén Martín, Ana Cuenca and Stephen L. Buchwald*

*Department of Chemistry, Massachusetts Instituteof Technology, Cambridge, Massachusetts 02139, Email: sbuchwalmit.edu

R. Martín, A. Cuenca, S. L. Buchwald, Org. Lett., 2007, 9, 5521-5524.

DOI: 10.1021/ol7024718 (free Supporting Information)


Abstract

A modular and practical synthesis of highly substituted oxazoles consists of a sequential copper-catalyzed amidation of vinyl halides followed by cyclization promoted by iodine. A wide variety of functionalized oxazoles and polyazoles can be obtained in a selective manner from simple and easily accessible precursors.

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Room Temperature Copper(II)-Catalyzed Oxidative Cyclization of Enamides to 2,5-Disubstituted Oxazoles via Vinylic C-H Functionalization

C. W. Cheung, S. L. Buchwald, J. Org. Chem., 2012, 77, 7526-7537.


Key Words

Oxazoles


ID: J54-Y2007-4120